Water → HCID 23347803, compound

HRID 1855721Notes

Reaction equation

HRID 1855721 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:7]([C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 7732P-AnisidineHCID 89094Ethyl 1-methyl-alpha-oxo-1H-pyrrole-2-acetate

Product 1

HCID 23347803HCID 23347803, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4.0 g ethyl 1-methylpyrrole-2-glyoxylate and 2.96 g p-anisidine in 20 ml toluene is added 24 mg p-toluenesulfonic acid. Heating at reflux for 4 days with water being removed with a Dean-Stark trap is followed by washing successively with aqueous hydrochloric acid, aqueous sodium bicarbonate and brine. After drying, evaporation of the solvent affords a dark solid. Recrystallization from isopropanol gives a 58% yield of ethyl α-(4-methoxyphenylimino)-1-methylpyrrole-2-acetate, m.p. 83°-85° C.

Workup

  1. temperatureHeating
  2. customremoved with a Dean-Stark trap
  3. washby washing successively with aqueous hydrochloric acid, aqueous sodium bicarbonate and brine
  4. customAfter drying
  5. customevaporation of the solvent
  6. customaffords a dark solid
  7. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-65b02630b98344b3b014bd51f488f160
Source dataset
uspto-grants-1980_08
Patent number
US04216150

Reaction notes

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